Pete Crow-Armstrong Girlfriend: Who Is Madeline Kennedy?

Hey there, Cubs fans and curious readers! If you’re wondering about the romantic life of Chicago Cubs star Pete Crow-Armstrong, you’re not alone. With his dazzling plays on the field and vibrant personality off it, it’s no surprise that fans are eager to know more about who holds a special place in the heart of this 24-year-old outfielder.

As of July 2026, Pete is dating Madeline Kennedy, who joined him as his plus-one on the red carpet at the 2026 MLB All-Star Game in Philadelphia. The relationship marks a new chapter for Pete, whose previous, widely followed romance with Hailey Lavelle appears to have ended sometime after their public run in 2025. Let’s dive into the details of their story, keeping things clear and trustworthy, while exploring what makes his new relationship notable and addressing the questions fans have about his love life, his past relationship, and a bit about his life beyond the diamond.

Who Is Pete Crow-Armstrong’s Girlfriend Now?

Pete Crow-Armstrong’s girlfriend is Madeline Kennedy, a Chicago-based client growth executive who works in digital marketing and business development. She turned heads at the 2026 All-Star Game red carpet in a sleek brown, one-shoulder satin dress, marking her public debut alongside Pete. Not much has been shared yet about how the two met or how long they’ve been together, as their relationship is still quite new to the public eye.

Who Is Madeline Kennedy?

Madeline Kennedy currently works as a client growth executive for the dining and quick-service-restaurant vertical at the marketing firm Epsilon, a role she’s held since joining the company in January 2023. Before that, she spent about a year as director of client operations at Aditude. Her professional background spans digital marketing, advertising technology, client operations, and public relations, according to her LinkedIn profile. Unlike Pete’s previous relationship, Kennedy’s public presence with Pete is brand new, so many personal details—her age, hometown, and how the couple met—remain unconfirmed.

What Happened With Hailey Lavelle?

Fans following Pete’s love life over the past couple of years will remember Hailey Lavelle, his previous girlfriend, who was a fixture at Cubs games and red-carpet events throughout 2024 and 2025. Pete and Hailey reportedly met at Vanessa Hudgens and Cole Tucker’s wedding in Tulum, Mexico, in December 2023, and their relationship became public by the following spring. Hailey, an esthetician based in Chicago, was known for her low profile despite frequently supporting Pete at games and marquee events, including the 2025 All-Star Game red carpet in Georgia.

Their relationship lasted roughly two years, with online chatter and entertainment outlets flagging breakup rumors earlier in 2026. Neither Pete nor Hailey has spoken publicly in detail about the split, and much of what circulated online was speculative. What is confirmed is that by the 2026 All-Star Game, Pete’s plus-one was Madeline Kennedy rather than Hailey, signaling the relationship had indeed ended.

Are Pete Crow-Armstrong and Madeline Kennedy Married?

No, Pete and Madeline are not married or engaged. Given that their relationship only recently became public, they appear to be in the early stages of dating rather than considering marriage. There’s no indication the couple has children together, either.

Pete’s Life Beyond Romance: A Rising Star Cements His Status

Born on March 25, 2002, in Sherman Oaks, California, Pete Crow-Armstrong turned 24 this year and has firmly established himself as one of MLB’s most exciting players. His breakout 2025 season was historic: he slashed .247/.287/.481 with 31 home runs, 37 doubles, four triples, 95 RBIs, 35 stolen bases, and 91 runs scored, joining Sammy Sosa as the only 30-30 (home runs/steals) players in Chicago Cubs history. He also won a Gold Glove, posted a 5.4 WAR, and drew MVP votes.

Defensively, Pete remains in a class of his own. He set a single-season record with 19 five-star catches (plays with a 0-25% catch probability), breaking a mark that had stood since Billy Hamilton’s 12 in 2016, and his outs above average ranked among the best in the sport.

That performance prompted the Cubs to lock him up long-term: in March 2026, Pete signed a six-year, $115 million contract extension running from 2027 through 2032, with no club options—making it notable as one of the largest such extensions for a player still years away from free agency. The deal includes a $5 million signing bonus and salary escalators tied to future MVP finishes. He played the 2026 season under a one-year, $894,000 salary before the extension kicks in, and appeared in his second consecutive All-Star Game in July 2026, this time in Philadelphia, where he pushed back on being labeled the “face” of the Cubs, saying he’s still learning to carry that kind of title.

Off the field, Pete’s personality continues to shine—from his bold style to his fan-friendly energy—drawing comparisons to Cubs fan favorites like Javier Báez and Kyle Schwarber.

Who Are Pete Crow-Armstrong’s Parents?

Pete’s family background adds another layer to his story. His parents, Ashley Crow and Matthew John Armstrong, are both actors, giving Pete a unique connection to the entertainment world. Ashley Crow is best known for her role as Sandra Bennet in the TV series Heroes, while Matthew John Armstrong appeared in shows like American Dreams. Their influence likely shaped Pete’s comfort in the spotlight, from his confident media interactions to his red-carpet presence.

Pete’s Contract and Net Worth

Pete Crow-Armstrong was selected 19th overall by the New York Mets in the 2020 MLB Draft before being traded to the Cubs in 2021. After making his big-league debut in September 2023, he blossomed into a franchise cornerstone, culminating in his six-year, $115 million extension signed in March 2026. With that deal now locking in guaranteed earnings through 2032—plus endorsement opportunities that have grown alongside his profile—estimates of his net worth have climbed well beyond where they stood during his rookie years, though exact figures aren’t publicly disclosed.

Why Fans Are Curious About Pete’s Love Life

It’s easy to see why fans stay invested in Pete Crow-Armstrong’s personal life. His rapid rise from a promising prospect to a two-time All-Star and franchise centerpiece has made him a household name in Chicago and beyond, and any change in his relationship status naturally draws attention. The shift from Hailey Lavelle to Madeline Kennedy has fans speculating and following along, even as both Pete and his new girlfriend have kept most details private so far.

Conclusion

Pete Crow-Armstrong’s off-field story has taken a new turn in 2026. After roughly two years with Hailey Lavelle, he’s now stepping out with Madeline Kennedy, who made her public debut alongside him at the All-Star Game red carpet in Philadelphia. Meanwhile, Pete’s on-field career keeps climbing new heights, headlined by a landmark $115 million extension with the Cubs. Whether it’s his next highlight-reel catch or the next chapter of his personal life, Pete Crow-Armstrong remains one of baseball’s most-watched young stars.